2-Butynoic acid

Base Information

• Chemical Name: 2-Butynoic acid
• CAS No.: 590-93-2
• Molecular Formula: C4H4O2
• Molecular Weight: 84.0746
• Hs Code.: 29161900
• European Community (EC) Number: 209-695-7
• NSC Number: 174116
• UNII: W3AM9ANZ22
• DSSTox Substance ID: DTXSID4060444
• Nikkaji Number: J6.755E
• Wikipedia: Tetrolic_acid
• Wikidata: Q30693372
• ChEMBL ID: CHEMBL4073377
• Mol file: 590-93-2.mol

Synonyms:2-butynoic acid;tetrolic acid

Chemical Property of 2-Butynoic acid

Chemical Property:

• Appearance/Colour: White to yellow powder
• Vapor Pressure: 0.117mmHg at 25°C
• Melting Point: 78-80 °C(lit.)
• Refractive Index: 1.3918 (estimate)
• Boiling Point: 203 °C at 760 mmHg
• PKA: 2.62(at 25℃)
• Flash Point: 90.9 °C
• PSA: 37.30000
• Density: 1.159 g/cm³
• LogP: 0.09430
• Storage Temp.: 2-8°C
• Solubility.: water: soluble50mg/mL, clear to very slightly hazy, colorless to
• Water Solubility.: Soluble in water. Slightly soluble in methanol and chloroform.
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 84.021129366
• Heavy Atom Count: 6
• Complexity: 112

Purity/Quality:

98%,99%, ^*data from raw suppliers

2-Butynoic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 34-20/21/22
• Safety Statements: 26-27-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC#CC(=O)O
• Uses: Synthon employed in a variety of reactions, including cycloacylation of phenols to flavones and chromones,1 and cyclization to γ-butyrolactones.2 2-Butynoic acid is used as an intermediate in organic synthesis and pharmaceuticals. It is used as a synthon in various reactions, which includes cylcoalkylation of phenols to flavones and chromones. It is involved in the cyclization of gamma-butyrolactones. It is also used in the synthesis of Z-trisubstituted olefins through μ-alkylation. It plays an important role in the preparation of chirally pure 1,2,3,4-tetrahydroisoquinoline analogs, which finds application as anti-cancer agents.

Technology Process of 2-Butynoic acid

There total 42 articles about 2-Butynoic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 91.0%

Ethyl 2-butynoate (4341-76-8) → 2-Butynoic acid (590-93-2)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; methanol; at 0 ℃;

DOI:10.1039/c8ob01328d

Reference yield: 82.0%

methyl propargyl alcohol (764-01-2) → but-2-ynal (1119-19-3) + 2-Butynoic acid (590-93-2)

Guidance literature:

With sodium hydroxide; sodium hypochlorite; sulfuric acid; TEMPOL; tetra(n-butyl)ammonium hydrogensulfate; Aliquat 336; In dichloromethane; water; at 5 - 10 ℃; pH=8 - 10;

Reference yield: 66.0%

1-trifluoromethanesulfonyloxyethyledenemalonic acid (725339-89-9) → 2-Butynoic acid (590-93-2)

Guidance literature:

With water; sodium hydrogencarbonate; at 20 ℃; for 12h;

DOI:10.1039/a901921i

upstream raw materials:

(Z)-1-propenyl bromide

(Z)-3-chloro-2-butenoic acid

(E)-3-chloro-2-butenoic acid

2,3-dichloro-crotonic acid

Downstream raw materials:

Ethyl 2-butynoate

3-Methylbicyclo<2.2.1>hepta-2,5-dien-2-carbonsaeure

(E)-β-methoxymethacrylic acid

(Z)-but-2-enoic acid

Refernces

• 1、 Xiao, Guorong,Wu, Kaifu,Zhou, Wei,Cai, Qian. "Access to Triazolopiperidine Derivatives via Copper(I)-Catalyzed [3+2] Cycloaddition/Alkenyl C?N Coupling Tandem Reactions". supporting information. p. 4988 - 4991. Retrieved 2021/10/14.
• 2、 -. "Preparation method of 2-butynoic acid". Paragraph 0050-0063. . Retrieved 2020/01/25.